Recently, I got together with two friends, Penny and Cathy, who I worked with for many years at the Anne Arundel County Office of Planning and Zoning. The three of us are now retired and had some serious catching up to do!

We decided to meet at noon on a weekday at Leeward Market Café and Pizzeria located at the corner of Chester Ave and 2nd Street in old Eastport. Coming in three cars, we were somewhat concerned about the parking availability, but found nearby parking on the street with ease.

Although none of us had ever been there, it turned out to be the perfect place for two major reasons. First, we were able to sit and talk for two hours without disapproving looks or anyone suggesting that we leave and second, the thin crust pizza was amazing.

The restaurant is typical of the old-fashioned corner store.

Here’s the set-up: the ordering area is the first room you come to when entering the restaurant. There’s a blackboard menu with regular offerings as well as specials, and also paper menus. The kitchen/prep area is within view. Down the hall in this narrow structure is a general store section with shelves of drinks, jars, boxes, and bottles of standard items. Beyond that is a cozy dining area that looks out on the backyard and the side street.

Two very friendly people greeted us and answered questions. Each of us ordered a 10 “ personal pizza ($5). There were many toppings offered for the additional charge of .50 each. I selected the spinach, fresh mozzarella, and roasted red pepper. Cathy chose the crumbled chorizo and roasted red pepper, and Penny had the pepperoni, feta, and artichoke hearts. The crust was thin and crispy and we ate every crumb.

In addition to pizza, Leeward specializes in breakfast, soups, salads, and special/deli sandwiches. I plan to return soon to sample the Eastport Veggie Wrap and the Mozzarella Classic. The breakfast wrap with scrambled eggs and whatever meats or veggies ‘your li’l heart desires’ sounds wonderful, too!

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About the Author - Lois Villemaire

Lois Villemaire, originally from the Philadelphia area, has resided in Annapolis for 40 years. She retired from the AA County Office of Planning and Zoning in 2007, and subsequently worked for several years for the Montgomery County Planning Department. Now that she and her husband are retired, they both enjoy their children and grandchildren, golfing, biking, yoga, reading and exploring around Annapolis. Lois currently serves on the City of Annapolis Planning Commission.